


Begging for a pegging

by Anonymous



Category: Pocket Monsters | Pokemon - All Media Types
Genre: Anal Sex, Cock & Ball Torture, Crossdressing, F/M, Femdom, Foot Fetish, Footjob, Pegging, Verbal Humiliation, femboy
Language: English
Status: Completed
Published: 2021-02-15
Updated: 2021-02-15
Packaged: 2021-03-16 22:40:50
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,808
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29461428
Author URL: https://archiveofourown.org/
Summary: Plumeria finds out that Gladion has a very kinky secret and makes a deal to keep it..but only if he begs her.
Relationships: Gladio | Gladion & Plumeri | Plumeria
Kudos: 4
Collections: Anonymous





	Begging for a pegging

Gladion stood naked in his room as he looked at the stolen clothing he had gathered carefully over the past week.

He looked in the mirror to take in what he looked like now. He was slender and hairless, no real muscle, and down below was his cock. It was smaller than average, he knew it and was just a little bit annoyed by that. Though at the same time he couldn’t help but think it was appropriate for himself with his interest.

And with that idea he picked up the bright pink thong that he picked up just yesterday. It had been the riskiest one. So he had put it off till last but it was also going to be the first one he’d put on. 

Next came the shirt that was a little too tight, and last was the skirt which was about a size too small to properly cover his crotch so the rather bulge small of his dick could be seen. He then slipped on a cap and wig..

Last was the usual Skull bandana over his face he looked in the mirror, other than the bulge in the bright pink panties and the totally flat chest in an overly tight skull shirt he looked just like one of the female grunts.

“Wow..I.look good in this.” he said in his best falsetto voice “I could really pass as a girl like this.”

“Yeah, you could.” Plumeria said from the doorway.

Whipping around the boy blushed enough that it went past his face cover.

“Wh..what are you doing?” he snapped trying to go back to his normal voice but his tone still cracked a little.

Plumeria smirked.

“A few girls have said that some clothes were missing.” she said “I kind of figured one of the guys was behind it. I have to say you were pretty low in my list of suspects.”

“So color me surprised when I find you here cross dressing.” she said walking in and closing the door behind herself.

“Though I gotta say..you do make a pretty cute girl.” she said reaching out and cupping the boy’s chin.

Gladion tried to slap her hand away but Plumeria just caught his wrist with her other hand and then grabbed his other wrist.

“Tell you what..a bunch of the girls are pretty ticked about their missing uniforms. If they found out they’d probably want to beat you up.” she said “But I’m willing to keep it a secret.”

“What do you want?” Gladion asked, he knew there was no way she would just do it out of the kindness of her heart. She played the big sister role a lot but she was for sure a harsh and serious woman when she wanted something.

“Oh, it’s simple.. “ she said licking her lips “I want to pound your cute little femboi ass.”  
Gladion just blinked.

“What?” he asked, a bit shocked by what he just heard.

“It’s simple.” she said “You are dressed like a girl, so I want to fuck you like one.”

Plumeria chuckled “I just love the way boys moan when I fuck them in the ass, the way their cocks twitch and squirt when I slam their prostate is just so damn hot.”

Gladion bit his lips under his mask, he was getting a little hard.

Plumeria noticed.

“I take that as a yes.” she said.

Gladion just nodded slowly. He hadn’t wanted to be caught like this but he couldn’t deny the idea of anal sex did turn him on a lot. He regularly did anal masterubation but just with his fingers so he was pretty limited in how deep he could easily get.

“Good girl.” Plumeria said.

Gladion’s small cock twitched getting hard enough to just peek out of the top of his panties.

“Just stay here.” Plumeria said as she reached down and flicked her fingertip against the head of Gladion’s dick making him yelp in a mix of mild pain and pleasure.

Plumeria left and returned quickly with two items in hand.

A bottle of lube and a strap on.

“On your knees, sissy.” she ordered.

Gladion gulped and obeyed.

As he got down Plumeria began to strip.

She slipped off her pants and panties showing her pussy to the boy like it was nothing, though he noted that had her pubes shaved into the skull logo, and that the skin around her crotch was a bit paler. He also got a good look at the entirety of her tattoo.

“Like what you see?” she asked as she pulled of her top to show that not only were they a little pale as well but her nipples were pierced with barbells that had skulls on the ends.

Gladion nodded.

“Well too bad you aren’t going to be touching them.” she said as she walked up to him and used her foot to lift his skirt. Taking a good look at his prick she laughed at it, not hiding her thoughts as she stared at it.

“Wow..that’s such a teeny tiny little thing.” she said as she began to rub it with her foot “There’s no way anyone would ever feel anything if you stuck it in them.” she mocked “Fucking seriously, it’s perfect for a girly boy like you.”

Gladion felt a flush of different emotions.

The mockery of his mini manhood set off some ange but even more than that it made him aroused as it grew stiffer and twitched a bit.

“Oh you like this?” Plumeria said “Which is getting you harder..getting made fun of or getting my foot all over the sad little thing you are trying to pass off as a dick?”

Gladion said nothing.

“Answer or…” she moved her foot down and started to put pressure on his smooth balls.

“Ah..” he gasped a little at the jolt of pain shot through his crotch “Owow..please…”

“Please step on them harder?” Plumeria asked as she started to put a bit more weight on Gladion’s tecticals. 

“Please..stop!” he panted out as his cock twitched and started to leak precum enough that it dribbled onto Plumeria’s foot.

“Why..seems like you like it.” she said as she ground her toes slowly making the pain worse and in spite of himself Gladion couldn’t help but moan. As much as it hurt there was no denying that a part of him was enjoying it.

Plumeria just laughed.

“Tell me that you are a panty thieving sissy that wants to get treated like a bitch.” she said “And really sound like you mean it!” she pressed down again making the boy whimper as he squirted more precum.

“I...I’m..I’m a panty thieving sissy boy who wants to have my ass fucked like a cheap bitch..please pound my asspussy!” he shouted.

Plumeria laughed.

“Haha, great you are such a little slut.” Plumeria said as she lifted her foot off of Gladion’s balls. He let out a sigh of relief but that turned into a moan of pain as right away she brought her heel down on his shaft crushing his dick fully underfoot.

The shock of it was enough to make him cum instantly.

As his cock pulsed and squirted under Plumeria’s foot she laughed.

“Mmmh..I love making little sissies cum like that.” she said as she lifted her foot, jizz all over the sole of it.

Gladion was whimpering in pain as Plumeria pressed her foot against his face smearing it with his own seed.

“Now stop crying and bend over hand on the wall and ass out.” She odred.

Gladion struggled to stand, the pain in his crotch was throbbing so bad he felt almost sick. But he couldn’t deny that he had never cum that hard before.

As he assumed the position he felt Plumeria slap his ass hard, the skirt rolled up enough to fully display it.

“Damn, you have a fatter ass than I thought.” Plumeria said “How do you keep it in them skinny jeans?” she asked as she slapped him more and more. Gladion was whimpering in pain as his tender white ass began to turn red from all the smacks. 

“Now beg, beg Big Sis Plumeria to pop your black cherry.”

“Please Big Sis Plumeria...fuck my virgin sissy boy butt. Make me into a woman by fucking me like a cheap whore.”

“This just keeps getting better and better.” she said as she poured lube all along her toy, stroking it for a few moments to get it properly coated. She then poured it down Gladion’s backside letting it run down his ass crack. 

The cool, wet lube on his raw and tender ass made him wince and moan.

Plumeria grabbed his hips hard and began to rub her faux cock against the twitching pucker of Gladion’s boy-pussy.

“Now..just relax and let big sis Plumeria in nice..and..” she pushed forward the tip spreading his asshole “deep!”

To emphasize the last part she slammed in down to the base in a single thrust. The shock of being filled all at once made Galdion cry out all at once. Not giving him a moment to adjust she began to pump her hips hard and fast. 

“Your little clitty is leaking like crazy.” Plumeria taunted as she reached down and rubbed her fingers along his sissy dick. He was oozing pre-cum like a broken faucet and could feel something bigger building rapidly.

“Good girl..now let’s hit the bitch button.” she said stopping for a second “No sissy can hold back when I slam it.”

Gladion was too lost in pleasure to fully understand what she was saying. Though as she suddenly pushed forward at a new angle he lost what tiny bit of sense he had managed to cling to.

There was a pressure and a shock like electricity that travel straight to his cock and in seconds Gladion had plastered the wall in the thickest load of cum he’d ever produced in his life. But again Plumeria didn’t give him a moment of rest as she suddenly wrapped one arm around his throat, lightly choking him as she used her other hand to grab his overly sensitive cock as hard and tight as she pumped it as hard and fast as she fucked him.

“You are going to be my new little fuck toy.” she said into his ear “Anytime, anywhere I want you’ll drop your pants and get ready for me to play with your boi-pussy.” She said as she made him cum again though nothing came out as she clenched the base of his shaft too tightly to allow it.

Gladion drunk on the pain, pleasure, humiliation, and bliss could only pant in response.

“Good girl.”Plumeria said as she kissed his ear.


End file.
